138213-44-2

Upstream product

• 138192-34-4 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-5-ethyluracil 
• 100-52-7 benzaldehyde 
• 165960-75-8 6-(acetoxyphenylmethyl)-1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-5-ethyluracil 
• 646-06-0 1,3-DIOXOLANE 
• 171048-63-8 6-benzyl-5-ethylpyrimidine-2,4(1H,3H)-dione 
• 444788-55-0 1-(2-acetoxyethoxymethyl)-6-benzyl-5-ethyluracil 
• 138192-35-5 1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxymethyl]-5-ethyl-6-(hydroxy-phenyl-methyl)-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Pyrimidine acyclonucleoside derivatives, preparation method and use thereof

The invention relates to a compound having general formula (I): wherein n is equal to 3; R1 is an ethyl or isopropyl group; each of the R2 groups is independently of each other a hydrogen atom, a C1-C3 alkyl group or a halogen atom; one of the R3 and R4 groups represents a hydrogen atom while the other of the R3 and R4 groups represents an OH or OR5 group, where R5 can be a C2-C7 acyl group, an alkyl(C1-C6)animo-carbonyl group, an aralkyl(C1-C6)aminocarbonyl optionally substituted on the aryl, an arylcarbonyl group optionally substituted or a heteroarylaminocarbonyl group. Said compound is particularly suitable as an antiviral agent and especially as an anti-HIV-1 agent.

Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2- hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents

Several 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6- (phenylthio)thymine (1; HEPT) were synthesized and evaluated for their anti- HIV-1 activity. LDA (lithium diisopropylamide) lithiation of 5-ethyluracil derivatives 7 and 8 and subsequent reaction with an aryl aldehyde gave 6- (arylhydroxymethyl)-5-ethyluracil derivatives 9-12. 6-(Arylhydroxymethyl)-5- isopropyluracil derivatives 15-18 were prepared from the 5-isopropyl-2- thiouracil derivatives 13 and 14 by the above procedure following oxidative hydrolysis of the thione. Preparation of the target 5-alkyl-1-(alkoxymethyl)- 6-benzyluracil derivatives 27-34 was carried out by acetylation of 9-14 followed by Pd-catalyzed hydrogenolysis. The 1-butyl- (37 and 39) and 1-(2- methoxyethyl)- (38 and 40) 5-alkyl-6-benzyluracils were synthesized by 1- alkylation of the 3-phenacyl derivatives 35 and 36 with alkyl halides followed by deprotection of the 3-phenacyl group. Compounds synthesized in this study inhibited HIV-1 replication in MT-4 cells in the submicromolar to nanomolar concentration range. From this series of compounds, 6-benzyl-1- (ethoxymethyl)-5-isopropyluracil (33) was selected for clinical evaluation.

Easy synthesis of 5,6-disubstituted acyclouridine derivatives

Ethyl 2-ethyl-3-oxo-4-phenylbutyrate is synthesized in a high yield from the corresponding benzyl cyanide and ethyl 2-bromobutyrate or by reaction of the potassium salt of ethyl 2-ethylmalonate with phenylacetyl chloride. Condensation of the 3-oxo ester w